Laurel Nakadate's work is risky, in every sense. Her boundary-crossing videos and photography are more than bold: they take her into potentially explosive situations. Over a decade ago, when she was an art student at Yale, she started making videos with men who hit on her in the street. These weren't her classmates, but rather guys from a fairly specific demographic: middle-aged singletons who lived alone and, though apparently not too shy to chat up a twentysomething, weren't exactly what you'd call socially at ease.

The artworks that came out of these encounters push all kinds of buttons. If the men first saw Nakadate as prey, things change once she got them on camera. The unsettling fantasies she asks them to perform with her, in their homes, include scenes where they pretend to attack her, or recite acts of misogynist violence, all the while looking far more awkward than we might feel watching them. The roleplay can also be silly and sweet – involving, for example, a make-believe birthday party or the imitation of cats and dogs. One memorably squeamish piece is an early work called Oops, in which the artist and three different men work through a dance routine to Britney Spears's Oops! … I Did It Again.

These aren't the kind of people you see on MTV. Even when both Nakadate and her subjects appear semi-nude, as they do in a number of videos, it's unsurprisingly the balding, lonely outsiders who seem vulnerable, not the gamine, self-assured artist. What the videos reveal about social exclusion, gender roles and the pernicious power of media representation proves these things are far from women-only issues. Questions arise about the slippage between art and life, between empathy and exploitation. Did these men really grasp what they were in for? Nakadate doesn't give us easy answers.

Her recent videos, photographs and movies have seen her mellow somewhat. The teenage girls who shake their booty in the mirror, as her heroines do in the feature film The Wolf Knife, or the young women posing defiantly beneath the Arizona desert's starry sky in her latest photography series, Star Portrait, tread similar terrain to Cindy Sherman's early dress-up fantasies or Larry Clark's cinema verite tales of troubled skater kids. Nakadate continues to probe how real people negotiate the images they are fed by movies, magazines and music, but these latest subjects seem anything but victims, taking on different roles on their own terms.

Why we like her: For her photo series 365 Days: A Catalogue of Tears. As an antidote to the "happy self-portraits people make day after day with their cellphone cameras and post on Facebook", Nakadate explores sadness, crying each day for a year and recording the results.

Cookie monster: Nakadate was a girl scout. She squeezed into her old uniform for a student work, selling cookies door to door while secretly filming people's reactions.